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Antifungal Drugs PHARMACOLOGY Antimicrobial Agents: Antifungal & Antiviral Drugs Dr. Uma Tekur Professor & Head Dept. of Pharmacology Maulana Azad Medical College New Delhi – 110002 (7-8-2007) CONTENTS Antifungal Drugs Amphotericin B Flucytosine Griseofulvin Azoles Nystatin Antiviral Drugs Antiherpese virus agents Other Antiviral Drugs Immunomodulators Antiretroviral Drugs Human Immune deficiency virus 1 Antifungal Drugs Fungal infections seen in human can be : a) Superficial fungal infections of skin, hair, nail, mucous membrane. These are due to: i) Dermatomycoses which causes ring worm or tinea infestation. These dermatophytes are Epidermophyton, Microsporum and Trichophyton, and are classified according to their site of infestation e.g.; Tinea Capitis (Scalp infection), TInea corporis (body infection), Tinea barbae (infection in the beard), Tinea cruris (infection in groin), Tinea pedis (also called athlete’s foot), TInea manum (infection in hands) and Tinea unguium (infection in the hairs). ii) Candidiasis (or often referred to as thrush) or infection caused by Candida spp affects chiefly the skin, oropharynx and vagina. Seen commonly in immune compromised patients e.g., in patients of AIDS, or with HIV infections, following the use of AMA’s over prolonged periods, and in patients of diabetes mellitus. iii) Pityrosporoum orbiculare causing Ptyriasis versicolor or Tinea versicolor. This is characterized by hyperpigmented macules, which are distinct with fine scaling. Commonly seen on the face, proximal extremities and in the oropharynx. iv) Sporothrix infection of cutaneous region seen as granulomatous lesion. These spread to distant region via the lymphatic system. b) Systemic fungal infection affecting deeper tissues and organs. These include the respiratory tract infection with candidiasis, cryptococcal meningitis and endocarditis, histoplasmosis infection common in the respiratory tract, coccidiomycosis, paracoccidiomycosis, pneumocystis carinii pneumonia all affecting the respiratory system. There has been an increase in the incidence of fungal infection during the past few decades. This increase may be attributed to : 1) An excessive or irrational use of AMA, which alter the pattern of the commensals in the body, leading to super-infection with the fungal infections, some of which are normally present as commensals. 2) A decrease in host defense mechanism as seen in patients of AIDS or patients on cancer chemotherapy, leading to iatrogenic fungal infections. 3) An increase in the use of immunosupprescent drugs also causes iatrogenic fungal infections. The antifungal agents include : 1. Antibiotics like a) polyenes, Amphotericin B, Nystatin, Hamycin, Natamycin and b) Heterocyclic Benzofurans like Griseofulvin 2. Antimetabolites: flucytosine 3. Azoles: Imidazoles, Clotrimazole, Miconazole, Econazole, Ketoconazole, Triazoles, Fluconazole iatraconazole. 4. Topical agents : Tolnaftate, Benzoic acid, undecyclenic acid, Quiniodochlor, Buclosamide, Haloprogin, Cyclopiroxolamine, Sodium thiosulphate. Drugs used in Systemic fungal infection Amphotericin B It is obtained from Streptomyces nodosus 2 Antifungal activity : The antifungal activity of amphotericin B includes Cryptococcus neoformans, Histoplasma capsulation, candida albicans, Blastomyces dermatitidis, Coccidoidies immitis, Aspergillus, Sporothrix Mechanism of action : It acts as a fungistatic drug in low concentration and as a fungicidal agent in high concentration. The polyene AMA binds with high affinity to ergosterol present in the fungal membrane. This binding leads to alteration in the cell permeability where in micropores are formed through which macromolecule and ions leak out of the cell leading to cellular death. Mammalian cell membrane has cholesterol (which resembles ergosterol) to which the polyene AMA binds with much less affinity. This accounts for the drug toxicity seen. Similarly bacterial cell wall lacks ergosterol and hence the polyenes AMA do not have activity against the bacteria. Resistance:Resistance to Amphotericin B is associated with alteration in the cells wall ergosterols. However, these alteration leads to a decrease in the virulence of the organism. Pharmacokinetics: Amphotericin B is not absorbed orally. Hence it is indicated for intestinal candidiasis. For systemic fungal infection Amphotericin B is administered intravenously as slow infusion. This is also available as liposomal preparation and as a lipid complex. These preparations selectively transfer the drug to the ergosterol in the fungal cell wall thereby decreasing the toxicity to the mammalian cells.This drug has a long t ½ of 15 days and is excreted slowly in the bile and urine. Clinical uses : i) Amphotericin B is used in most systemic infection including histoplasmosis, invasive aspergillosis blastomycosis and in fungal infection in immune compromised patients or patients with AIDS. However, Ketoconazole is preferred to amphotericin B because of its lower toxicity. ii) Polyene antibiotics can also be used topically as creams or as 3% lotion; as ointment to treat cutaneous and oropharyngeal candidiasis. Eye drops are used for mycotic infections of the eye. It is also used topically for vaginal and otomycosis. iii) Amphotericin B is used as a reserve drug for mucocutaneous Leishmaniasis and in resistant cases of Kala Azar. (This is not a fungal infection) Dose : 0.5 – 0.6 mg/kg/day as slow I.V. infusion in glucose upto a total dose of 2 gm. For systemic fungal infection 250 mg/kg daily; if tolerated, the dose is increased to 1 mg/kg over 4-6 hrs. It is important to administer a test dose in all patients. Adverse effects: Amphotericin B is a toxic drug causing impairment of both hepatic and renal function. Hepatic function impairment can lead to the development of jaundice and renal toxicity is manifested as tubular necrosis, azotemia and irreversible renal damage. These adverse effects are dose dependent. Liposomal dosage form of amphotericin B has lesser incidence of renal toxicity. 3 Intravenous administration of amphotericin B can cause chills, fever, vomiting, headache, and thrombophlebitis in the injected vein. Severe reaction may be treated with Paracetamol, an antihistamine and corticosteroids. Topically administered amphotericin B is usually well tolerated except for an occasional yellow discoloration of the skin. Flucytosine Flucytosine is also called 5-flurocytosine or 5-FC. This is a pyrimidine antimetabolite and is structurally similar to the anticancer drug 5 flurouracil. 5 -FC however, does not have any anticancer activity. Mechanism of action : 5 -FC is taken up by the fungal cells where it is converted to 5 flurouracil by the fungal enzyme cytosine deaminase. 5 Flurouracil is further converted to 5 flurodeoxyuridine monophosphate. This compound is a competitive inhibitor of thymidylate synthetase. Thus ultimately the synthesis of DNA is inhibited. 5 FC has a greater selectivity of action against the fungal cells, as the mammalian cells are virtually devoid if cytosine deaminase. Pharmacokinetics : Flucytosine is well absorbed orally and is widely distributed in the body tissue including the CSF. It has a plasma t 1/2 of 3-6 hrs. It is excreted unchanged in the urine and hence to avoid accumulation of the drug in the tissues, the dose of 5 FC needs to be adjusted in patients with renal impairment Clinical use : It has been observed that when 5 FC is used alone, resistance develops rapidly. Hence it is advisable to give 5 FC along with amphotericin B. It is useful in disseminated candidiasis, aspergillosis, cryptococcosis when it is used in combination with amphotericin B. As this is synergistic effect, amphotericin B may be given in lower dose (see above for dose of amphotericin B) Adverse effects : ¾ 5 FC is relatively a non toxic drug. ¾ Nausea, vomiting epigastric distress and skin rash may be seen. In addition rarely 5 FC may cause bone marrow suppression leading to thrombocytopenia and leucopenia. Hence, 5 FC should be avoided in patients with terminal HIV infection. ¾ In addition, as 5-FC is administered along with amphotericin B, a nephrotoxic drug, close monitoring of patient with renal impairment is imperative. 5-FC has a narrow therapeutic window and hence it is important to keep the dose on the lower side, as higher doses of 5 FC may lead to a greater incidence of toxicity. Griseofulvin Griseofulvin is the first orally effective antifungal agent to be identified. The source of griseofulvin is Penicillin griesofulvium Mechanism of action : Griseofulvin interferes with the mitosis of the actively multiplying fungi. By combining with the microtubules of the actively dividing fungal cells, the drug disrupts the mitotic spindle and arrests the fungal mitosis in the metaphase. In addition griseofulvin binds to the newly synthesized keratin, especially around the tinea infected cells. This Keratin now 4 becomes resistant to fungal invasion. Therefore, the treatment of infection will depend on the site of infection, the cellular turnover and thickness of the keratin. Pharmacokinetics : The absorption of griseofulvin from the GIT is irregular. Griseofulvin is ineffective when applied locally. Presence of fatty food in the GIT increases its absorption. The plasma t½ is 24 hrs. However, as it gets bound to the Keratin, it is retained for weeks in the skin. Clinical use :It is administered systemically to treat dermatophytes including Microsporum, Trichophyton and Epidermophyton. As mentioned above, duration of treatment depends on the site of fungal infection e.g.; for
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